32 To Do: Chicago Blues Fest, Puerto Rican Day Parade, Dead & Company top things to do this weekend

Chicago is gearing up for another action-packed weekend as festival season takes the Windy City by storm.

From the iconic Chicago Blues Festival and the vibrant Puerto Rican Day Parade to the legendary Grateful Dead performing at Wrigley Field, the city is buzzing with an array of events. With a lineup that includes concerts at Northerly Island, diverse fairs and festivals, soccer matches, and the ever-enthralling Chicago White Sox games, residents and visitors alike can expect an eventful and lively weekend ahead in the neighborhoods of Chicago.

Chicago Blues Music Festival in Millennium Park

Toronzo Cannon performs on stage at The Chicago Blues Festival on June 9 2019 in Chicago, Illinois, United States. (James Fraher/Redferns / Getty Images)

The Chicago Blues Festival is held in Millennium Park, with 42 performances and over 100,000 expected attendance over the four-day period.

Thursday, June 8, 5:30 p.m. to 9 p.m.
Friday, June 9 – Sunday, June 11, 12 p.m. to 9 p.m.

Puerto Rican Festival

Fiestas Patronales Puertorriqueñas will be held in Humboldt Park at 2800 W. Division and 1400 N. Humboldt Dr. The event is located in what is now known as "Puerto Rico Town" on Division Street where the Annual Puerto Rican Day People’s Parade will also take place on Saturday, June 10.  There will be an entrance fee for those over 12 years of age from Friday through Sunday.

Thursday, June 8 and Friday, June 9, 4 – 10 p.m.
Saturday, June 10 and Sunday, June 11, noon – 10 p.m.

Puerto Rican Day People’s Parade

Parade Performers in traditional costumes leave the parade route during the Chicagos 41st Annual Puerto Rican Pride Parade in Humboldt Park Chicago, on June 15, 2019. (Jim Vondruska/NurPhoto via Getty Images / Getty Images)

The Puerto Rican Day People’s Parade assembles at 11 a.m. on Western Avenue from Augusta Blvd. to Division and proceeds westbound on Division from Western to Sacramento and disbands on Sacramento from Augusta to Division.

Saturday, June 10
2 p.m.

Heatwave Music Festival - Huntington Bank Pavilion (Northerly Island)

This two-day event is a music festival with the sounds of globally leading dance music.

Saturday, June 10 – Sunday, June 11
2 p.m. to 11 p.m.

Dead & Company Concert at Wrigley Field

A view of the crowd at the Hella Mega Tour at Wrigley Field on August 15, 2021 in Chicago, Illinois. (Timothy Hiatt/Getty Images / Getty Images)

The Dead & Company return to Wrigley Field this weekend with shows held inside the ballpark at Wrigley Field and is a ticketed event.

Friday, June 9 – Saturday, 10 June 2023
Gates open at 5 p.m., Show starts at 6:30 p.m.

Old Town Art Fair

The Old Town Art Fair is at the Old Town Triangle Historic District, 1763 N. North Park Avenue. The event features 200+ artists, a garden walk, live music, food court and Childrens Corner with an estimated 30,000 attendees.

Saturday, June 10, 10 a.m. – 7 p.m.
Sunday, June 11, 10 a.m. – 6 p.m.

Chicago White Sox at Guaranteed Rate Field

A general view of Guaranteed Rate field during the game between the Chicago White Sox and the Cleveland Guardians at Guaranteed Rate Field on July 22, 2022 in Chicago, Illinois. (Quinn Harris/Getty Images)

Friday 7:10 p.m. Country Music Night)
Saturday 1:10 p.m. (Hawaiian Shirt)
Sunday, 1:10 p.m. (Family Day) vs Miami Marlins

Wells Street Art Fair

Located on Wells Street between North Ave and Division. An estimated 50,000 attend this popular art festival featuring stage performance, local music, performance artists and tribute bands.

Saturday, June 10 and Sunday, June 11
10 a.m. to Dusk

Chicago Fire vs Columbus Crew at Soldier Field

A general view of Soldier Field is seen during a game between the Los Angeles Galaxy and the Chicago Fire on April 16, 2022 at Soldier Field in Chicago, IL (Robin Alam/Icon Sportswire via Getty Images / Getty Images)

Arrive early and expect increased traffic with the Heatwave Music Festival happening at Northerly Island!

Saturday, June 10, 7:30 p.m.

Andersonville Midsommarfest

The Andersonville Midsommarfest is located on Clark St. from Foster to Gregory (just north of Catalpa) featuring stages for music, food and more. Streets are closed for the event.

Friday, June 9, 5–10 p.m.
Saturday, June 10
Sunday, June 11, noon–10 p.m.

Navy Pier Fireworks

Fireworks go off over Navy Pier on Saturday, July 4, 2015, in Chicago. (Armando L. Sanchez/Chicago Tribune/Tribune News Service via Getty Images / Getty Images)

Navy Pier will present fireworks show on Saturday and continues each Wednesday and Saturday through Labor Day weekend. Saturday shows begin at 10 p.m.

Saturday, June 11
10 p.m.